Ethyl propiolate → HCID 178472242, compound

HRID 624636Notes

Reaction equation

HRID 624636 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[NH:9])[NH:7][OH:8])=[C:4]([F:12])[CH:3]=1.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[C:14]#[CH:15]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[NH:9])[NH:7][O:8][CH:15]=[CH:14][C:13]([O:17][CH2:18][CH3:19])=[O:16])=[C:4]([F:12])[CH:3]=1

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 178513246HCID 178513246, compound2×

Product 1

HCID 178472242HCID 178472242, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-Bromo-2-fluoro-N-hydroxybenzimidamide 24 (800 g, 3.43 mol, 1 eq) and Amberlyst® A21 (20 wt %, 160 g) in PhMe (12 L, 15 vol) was added ethyl propiolate (471 g, 4.8 mol, 1.4 eq) at 10° C. The reaction was stirred at 50° C. overnight and checked by LC-MS (ca 14A % of starting material 24 was left). Reaction was then filtered and the filtrate was concentrated under vacuum, and 1015 g ethyl 3-(4-bromo-2-fluorobenzimidamidooxy)acrylate 25 was obtained as a yellow oil with 84.9% LC purity (yield: 89%).

Workup

  1. customReaction
  2. filtrationwas then filtered
  3. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-c4de70227cd84b2d926c7f12f22c7ee2
Source dataset
uspto-grants-2016_04
Patent number
US09303043B2

Reaction notes

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